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Triethylamine → 2-(4-Chloro-3,5-dimethoxyphenyl)-4-hydroxymethylpyridine

HRID 984165
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 984165
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=2)[C:13](O)=[O:14])=[CH:4][C:3]=1[O:19][CH3:20].C(N(CC)CC)C.ClC(OCC)=O>C1COCC1>[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][N:18]=2)=[CH:6][C:7]=1[O:8][CH3:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 225580392-(4-Chloro-3,5-dimethoxyphenyl)isonicotinic acid

Produkt 1

HCID 225579712-(4-Chloro-3,5-dimethoxyphenyl)-4-hydroxymethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of 2-(4-chloro-3,5-dimethoxyphenyl)isonicotinic acid (7.20 g) and triethylamine (5.6 mL) in THF (70 mL) was added ethyl chloroformate (2.8 mL). The mixture was stirred at room temperature for 1 hour and filtered. To the filtrate was then added a solution of sodium borohydride (1.25 g) in water (4 mL). The mixture was stirred at room temperature for another hour and evaporated. Water was added to the residue and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was subjected to silica gel column chromatography using chloroform-methanol (20:1) and then chloroform-methanol (15:1) to give the title compound.

Aufarbeitung

  1. filtrationfiltered
  2. additionTo the filtrate was then added a solution of sodium borohydride (1.25 g) in water (4 mL)
  3. stirringThe mixture was stirred at room temperature for another hour
  4. customevaporated
  5. additionWater was added to the residue
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b78643f1b0c6411da5f16cee794c5037
Quelldatensatz
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06867221B2

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